Interview: The man driving Skype's strategy

Christopher Dean, chief strategy officer at web telephony firm Skype, discusses his career and offers tips for building a winning strategy

Christopher Dean is chief strategy officer at Skype. He owns corporate strategy, and runs an innovation group called SkypeWorks. Winning is his big motivation. Dean says, "I like to win. And I think I'm competitive that way, so, that's clearly something that motivates me on a daily basis.

"I really do love technology and I love to consume technology and use technology. And in my lifetime, it's changed the world as we know it and I think it will continue to. So, having a job in and around and enabling new technologies that can continue that change is something that gets me up every day."


A strong team is essential to his strategy. Dean says he looks for and tries to build a strong meritocracy in his team. "I expect people to work very hard, leave their body on the field and we will reward people, on a merit basis, who deliver."

He runs a small functional team, which works on a project-to-project basis. Dean says, "People have to be able to get up to speed quickly and manage and understand the new topics that they're facing."

But what makes a good team player? Dean points out that different people are selected for different roles. "A business development guy has got to be a deal-doer. He needs to understand how to manage the relationship, close the relationship and implement the relationship. And that closer in a business development or a corporate development role is a very different person from that director of strategy, who is running one of our corporate strategy projects."

Start-ups versus major players

Dean started his working life in venture, before starting his own business and working in many other start-ups. He says one thing that would help him to be appreciated would be to add a high-value brand in his CV, such as being able to say he had worked for Apple Computer or for Cisco.

"You need to view yourself as a product that people are buying as a service. And if you've got that brand, that experience in your background, I think that people value that [you've worked for] a recognisable company versus a string of five startups that no one has heard of."

Dean believes the companies that are leaders have good internal practices. He says, "You can actually learn in a structured format there. Rather than going out and teaching it all to yourself, go someplace that has a great set of best-practices and learn from those experiences. And those, typically, tend to be successful, large, big-branded companies."

Career advice

The best career advice that Dean was ever been given was when he was at Kellogg business school. The chairman of Morgan Guaranty Insurance advised him to put a plan in place. Dean says, "You have to have a three to five year plan for your life personally and your career. And then, you need to reassess that plan on an annual basis."

This means people need to have certain financial goals. They also need certain career goals and certain family goals. Dean says, "Write it down and then look at it every year. Are you achieving those goals? Have some of those goals been modified or changed?"

As a final piece of advice, he says, "Many people just arbitrarily make their way through life. So creating a plan and thinking for the future was probably one of the best pieces of career advice and family advice and life advice I have ever had."

This article is based on an interview from Watch the interview with Christopher Dean in full.

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